Dimethyl Sulfate → Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetate

HRID 1700026Notes

Reaction equation

HRID 1700026 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)=[O:6].[C:19](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(#N)C>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([O:16][CH3:19])=[O:15])=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 109235672-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid

Product 1

HCID 10062338Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetateYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Mix 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-propionic acid 10.0 g, 37.3 mmol) and anhydrous potassium carbonate (3.5 g, 25.3 mmol). Heat to 40° C. in acetonitrile (100 mL) and stir under a nitrogen atmosphere. Add dimethyl sulfate (13.3 g, 105 mmol) and reflux for 45 minutes. Evaporate the solvent in vacuo, dissolve the residue in ethyl acetate (50 mL) and wash with water (4×50 mL). Dry (MgSO4), filter through silica gel and evaporate the solvent in vacuo to give the title compound (6.4 g, 89%).

Workup

  1. customEvaporate the solvent in vacuo
  2. dissolutiondissolve the residue in ethyl acetate (50 mL)
  3. washwash with water (4×50 mL)
  4. dry with materialDry (MgSO4)
  5. filtrationfilter through silica gel
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-d68f7a0d5d26498caf5845d44e1c0e3d
Source dataset
uspto-grants-2002_02
Patent number
US06348597B2

Reaction notes

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